9 of The Friendliest Towns on the Chesapeake Bay
People flock to the Chesapeake Bay from all across the world, and for good reason. Chesapeake is the largest estuary in the nation where waters from inland rivers meet with the Atlantic Ocean and where vacationers have met with relaxation and fun for years. Its glimmering surface is a jewel in the Mid-Atlantic which is known for its world-class fishing and astounding natural beauty. These nine towns found on the Chesepeake Bay are perfect for exploring its natural beauty, amazing seafood and their hospitality.
Cambridge, Maryland
Found on the state’s Eastern Shore in 1684, Cambridge is known as one of Maryland’s oldest colonial cities. This charming town has a grand maritime heritage as a seaport community built on the Choptank River, which can be explored through the town’s heritage museums. That said, Cambridge is best experienced in three dimensions. Take the town by storm and see it through one of the many river cruises and district tours available. The town also has a burgeoning nightlife beyond the shoreline. Visit High Street, called one of the most beautiful in the nation by author James Michener, or the Blackwater National Wildlife Refuge. Lastly, be sure to taste the oysters, crabs, and fish that were crucial to the town’s prosperity at its founding and remain an integral part of Cambridge’s lifeblood today.
Cape Charles, Virginia
This family-friendly beach town on Virginia’s cape offers something for everyone, especially photography enthusiasts. For those seeking the perfect shot, Cape Charles is ideal for photographers. Stop at Peach Street Books to explore what might be the cutest bookstore in the Mid-Atlantic, with baked goods and coffee always available. Relax in the deep blue waters of the bay and end your day with a creative twist on a classic at Buskey Cider. They craft seasonal ciders from fresh Virginia apples, including flavors like Habanero Mango and Watermelon Rosemary. For dining, try the Hook at Harvey. Tip: reserve a table outside for the best sunset views.
Chesapeake City, Maryland
Beautifully maintained Victorian and Colonial-era homes await down by the bay in Chesapeake City. Traipse along the Ben Cardin C&D Canal Trail to take it in at the water’s edge. The town has worked hard to preserve its 19th-century feel, and it shows. Narrow streets and knickknack shops give the town a distinct seaside atmosphere. The town’s historic district is full of brickwork, with many of the homes dating to the 1800s. Chesapeake City is also built on one of the largest working commercial canals in the world. Visitors and residents alike are treated to a full view of outgoing ocean-bound ships. The town has a variety of companies that offer aquatic tours for those who wish to see the bay’s traffic up close.
Chestertown, Maryland
This historic college town on the banks of the scenic Chester River is full of small-town charm. From the extensive red brickwork along Chestertown’s streets to the natural beauty of the river, Chestertown is an underrated yet impressive addition to any list about the Chesapeake Bay. Every first Friday of the month, residents gather downtown to shop, enjoy wine, and mingle outdoors, browsing local merchandise. Alternatively, rent a kayak and paddle up the Chester for a relaxing change of scenery. Nature enthusiasts will love the Patapsco-McKeldin Loop in Patapsco Valley State Park. Before leaving, be sure to visit Evergrain Bread Company for some delicious, mouthwatering croissants.
Irvington, Virginia
It has been said that Virginia is for lovers, and the town of Irvington, in particular, has a lot to love. A quintessential piece of Americana, this town of roughly 400 was named one of the 20 best places to live on the coast by Coastal Living Magazine in 2020, and it is easy to see why. White picket fences and billowing sails on the Rappahannock River abound in Irvington. Enjoy prime bay-to-table dining and pedal around this quaint shoreline town in Virginia’s river realm. Watch sailboat racing at the annual Turkey Shoot Regatta from the shore for an exhilarating evening. Want to try sailing? Home to one of the East Coast’s premier sailing schools, Irvington is the perfect place to learn the ropes.
Onancock, Virginia
Tucked between the Chesapeake Bay and the Atlantic Ocean, Onancock was called “the Gem of the Eastern Shore” by Captain John Smith, the famous English explorer in the 1600s. Today, this vibrant town of 1,500 is chock-full of attractions and more than holds its own against the other entries on this list. Travel up Onancock Creek by kayak to a local winery, then visit the island of Tangier from the town’s port. Revel in a thriving art scene on the Chesapeake Bay at the town’s live theater, which has hosted performances for more than 35 years. See a performance by Main Stage Productions before stopping by one of the many artisan studios Onancock has. Apparently, something about the town and the nearby bay inspires artistic expression, and it is easy to see why.
St. Michaels, Maryland
Maryland is known for its succulent seafood and the inviting town St. Micheals is an excellent place to try it. The Maryland blue crab is renowned for its delicious, fatty meat and one would be hard pressed to find a restaurant in town where this crustacean was not on the menu. If oysters are preferred, try an oyster harvesting tour and get elbow-deep in a centuries-old tradition on the Eastern Shore. Sail Selina II comes highly recommended while in St. Micheals and is a wonderful way to spend an evening. The company offers cruises out into the bay on a gorgeous mahogany Roaring 20s era boat. Only a short drive away from St. Michaels, Tilghman Island is a small island which beckons visitors for a day in the natural beauty Maryland has to offer. Enjoy birdwatching, fishing and kayaking on an island with a reputation for top-notch hospitality.
Urbanna, Virginia
For seafood aficionados traveling to the Chesepeake Bay, a visit to Urbanna should be on the docket. This town of pretty, manicured streets along the Rappahannock River is home to the state’s largest oyster festival every November. The Urbanna Seafood & Raw Bar does offer half shell oysters year-round, however, but this town has so much more in store than shellfish. Walk the docks and listen to the sound of lapping waves, wander the quiet streets until sunset when the water comes alight in orange glow. This town boasts “more boats than folks,” and is an exemplary way to destress and decompress into the island groove (at least when the oyster festival is not on).
Rock Hall, Maryland
What started as a quiet town on the Chesapeake Bay has evolved into a boater's haven. Situated at the Chester River's mouth, this community of fewer than 1,500 residents features over 10 marinas, a yacht club, and excellent sailing opportunities. Visit Ferry Park to enjoy Rock Hall’s charming small beach and get a stunning sunset view of the bay. Sample innovative dishes like fruit pizza at the well-known Dockside Cafe or grab a root-beer float at Durding’s Store. The town has a distinctive fishing village vibe. To explore, begin on Main Street and head toward the Waterman’s Museum to learn about Rock Hall’s history.
There is no wrong way to explore the Chesepeake Bay. Truly, when it comes to seeing the charm and inviting hospitality of these towns along the estuary, the only question should be: where to start? Dining on the waterfront has never seemed so good. Delicious Maryland Blue Crab, endless oysters are the least of what Maryland and Virginia have to offer to their visitors. From birdwatching to sailing to doing nothing at all on quiet, tucked away beaches, it is safe to say the Chesepeake Bay has something for everyone.
